DMDM hydantoin

Last updated
DMDM hydantoin
DMDM hydantoin.svg
Names
Preferred IUPAC name
1,3-Bis(hydroxymethyl)-5,5-dimethylimidazolidine-2,4-dione
Other names
1,2-Dimethylol-5,6-dimethylhydantoine
Glydant
Identifiers
3D model (JSmol)
AbbreviationsDMDMH
ChemSpider
ECHA InfoCard 100.026.566 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 229-222-8
PubChem CID
UNII
  • InChI=1S/C7H12N2O4/c1-7(2)5(12)8(3-10)6(13)9(7)4-11/h10-11H,3-4H2,1-2H3 Yes check.svgY
    Key: WSDISUOETYTPRL-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C7H12N2O4/c1-7(2)5(12)8(3-10)6(13)9(7)4-11/h10-11H,3-4H2,1-2H3
    Key: WSDISUOETYTPRL-UHFFFAOYAB
  • O=C1N(C(=O)C(N1CO)(C)C)CO
Properties
C7H12N2O4
Molar mass 188.18 g/mol
Hazards [1]
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H302
P301+P312
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

DMDM hydantoin is an antimicrobial formaldehyde releaser preservative with the trade name Glydant. DMDM hydantoin is an organic compound belonging to a class of compounds known as hydantoins. It is used in the cosmetics industry and found in products like shampoos, hair conditioners, hair gels, and skin care products. [2] [3]

DMDM hydantoin slowly releases formaldehyde and works as a preservative by making the environment less favorable to microorganisms.

Safety

A patch test study found that "an increase in the use of DMDM hydantoin in cosmetic products will also inevitably increase the risk of cosmetic dermatitis in consumers allergic to formaldehyde." [4]

The safety of formaldehyde is a topic of ongoing concern, given the prevalence of formaldehyde and formaldehyde releasers in industrial uses. Formaldehyde is considered "an important metabolic product in plants and animals (including humans), where it occurs in low but measurable concentrations." [5] However, long-term exposure to formaldehyde (particularly routine inhalation of its fumes) is thought to cause irritation of the eyes and mucous membranes, [6] headaches, shortness of breath, and aggravation of asthma symptoms. [7] [8] It was declared a "toxic product" by the 1999 Canadian Environmental Protection Act, [9] and the US National Toxicology Program officially classed formaldehyde as "known to be a human carcinogen in June 2011. [10] [11] [12]

In the EU, the maximum allowed concentration of formaldehyde in finished products is 0.2%, and any product that exceeds 0.05% has to include a warning that the product contains formaldehyde. [13]

Related Research Articles

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Methylchloroisothiazolinone, also referred to as MCI, is the organic compound with the formula S(C2HCl)C(O)N(CH3). It is a white solid that melts near room temperature. The compound is an isothiazolinone, a class of heterocycles used as biocides. These compounds have an active sulphur moiety that is able to oxidize thiol-containing residues, thereby effectively killing most aerobic and anaerobic bacteria. MCI is often used in combination with methylisothiazolinone, a mixture known as Kathon. The isothiazolinones have attracted attention because they can cause contact dermatitis. Methylchloroisothiazolinone is effective against gram-positive and gram-negative bacteria, yeast, and fungi.

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<span class="mw-page-title-main">Cosmetics</span> Substances applied to the body to change appearance or fragrance

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<span class="mw-page-title-main">Diazolidinyl urea</span> Antimicrobial preservative used in cosmetics.

Diazolidinyl urea is an antimicrobial preservative used in cosmetics. It is chemically related to imidazolidinyl urea which is used in the same way. Diazolidinyl urea acts as a formaldehyde releaser.

<span class="mw-page-title-main">Isothiazolinone</span> Chemical compound

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<span class="mw-page-title-main">Imidazolidinyl urea</span> Chemical compound

Imidazolidinyl urea is an antimicrobial preservative used in cosmetics. It is chemically related to diazolidinyl urea which is used in the same way. Imidazolidinyl urea acts as a formaldehyde releaser.

<span class="mw-page-title-main">Formaldehyde releaser</span> Chemical compound used as a preservative that slowly releases formaldehyde.

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<span class="mw-page-title-main">Iodopropynyl butylcarbamate</span> Chemical compound

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References

  1. ↑ "GESTIS-Stoffdatenbank 1,3-Bis(hydroxymethyl)-5,5-dimethylimidazolidin-2,4-dion". gestis.dguv.de.
  2. ↑ DMDM hydantoin in the Consumer Product Information Database
  3. ↑ DMDM Hydantoin at sci-toys.com
  4. ↑ de Groot AC, van Joost T, Bos JD, van der Meeren HL, Weyland JW (1988). "Patch test reactivity to DMDM hydantoin. Relationship to formaldehyde allergy". Contact Dermatitis. 18 (4): 197–201. doi:10.1111/j.1600-0536.1988.tb02802.x. PMID   3378426. S2CID   221577901.
  5. ↑ Franz, Adam W.; Kronemayer, Helmut; Pfeiffer, Daniel; Pilz, Roman D.; Reuss, Gänther; Disteldorf, Walter; Gamer, Armin Otto; Hilt, Albrecht (2016), "Formaldehyde", Ullmann's Encyclopedia of Industrial Chemistry, American Cancer Society, pp. 1–34, doi:10.1002/14356007.a11_619.pub2, ISBN   978-3-527-30673-2 , retrieved 2021-07-03
  6. ↑ "Safety and Health Topics | Formaldehyde | Occupational Safety and Health Administration". 2019-04-11. Archived from the original on 2019-04-11. Retrieved 2021-07-03.
  7. ↑ "Notice of Adoption of Air Toxics Hot Spots Program Technical Support Document for the Derivation of Noncancer Reference Exposure Levels and 6 RELs | OEHHA". 2019-03-23. Archived from the original on 2019-03-23. Retrieved 2021-07-03.
  8. ↑ Canada, Health (2012-03-29). "Formaldehyde in your home". www.canada.ca. Retrieved 2021-07-03.
  9. ↑ "Health Canada - Proposed residential indoor air quality guidelines for formaldehyde". Health Canada. April 2007. Archived from the original on 2013-05-30. Retrieved July 3, 2021.
  10. ↑ Harris, Gardiner (2011-06-10). "Government Says 2 Common Materials Pose Risk of Cancer". The New York Times. ISSN   0362-4331 . Retrieved 2021-07-03.
  11. ↑ "Report on Carcinogens (RoC) - National Toxicology Program". 2011-06-08. Archived from the original on 2011-06-08. Retrieved 2021-07-03.
  12. ↑ "National Toxicology Program: 14th Report on Carcinogens". National Toxicology Program (NTP). Retrieved 2021-07-03.
  13. ↑ Groot, Anton C. de; Flyvholm, Mari-ann; Lensen, Gerda; Menne, Torkil; Coenraads, Pieter-Jan (2009). "Formaldehyde-releasers: relationship to formaldehyde contact allergy. Contact allergy to formaldehyde and inventory of formaldehyde-releasers". Contact Dermatitis. 61 (2): 63–85. doi:10.1111/j.1600-0536.2009.01582.x. hdl: 11370/c3ff7adf-9f21-4564-96e0-0b9c5d025b30 . ISSN   0105-1873. PMID   19706047. S2CID   23404196.
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